CN102408415A - Preparation method of mangiferin - Google Patents
Preparation method of mangiferin Download PDFInfo
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- CN102408415A CN102408415A CN2010102924650A CN201010292465A CN102408415A CN 102408415 A CN102408415 A CN 102408415A CN 2010102924650 A CN2010102924650 A CN 2010102924650A CN 201010292465 A CN201010292465 A CN 201010292465A CN 102408415 A CN102408415 A CN 102408415A
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Abstract
The invention relates to the field of pharmaceutical chemistry and discloses a preparation method of mangiferin. The preparation method of the mangiferin comprises the following steps: extracting mango fruits, mango leaves, mango skin and rhizoma anemarrhenae rootstock which are utilized as raw materials by utilizing a mixed solution of alcohol and water; filtering, condensing the filtered solution and extracting the obtained concentrated solution with an organic solvent; then crystallizing the extracted water phase; and recrystallizing with a mixed solution of acetone and water, thus obtaining the mangiferin. According to the preparation method of the mangiferin, macroporous resin is not used for purification, so that the resin pretreatment, adsorption and elution process can be avoided, the production period is shortened, the transfer rate is improved, the usage amount of the organic solvent is reduced, the production cost is reduced, and the environmental pollution is reduced. The mangiferin prepared by the preparation method of the mangiferin disclosed by the invention is high in purity, does not contain benzene organic solvents and is high in safety.
Description
Technical field
The present invention relates to the pharmaceutical chemistry field, relate to a kind of preparation method of Mangiferin specifically.
Background technology
Mangiferin (mangiferin) is claimed mangiferin again, the tabernaemontanus bulrush asphonin, and molecular formula is C
19H
18O
11, molecular weight 422 is for CAS number: 4773-96-0, and chemical structural formula is:
Mangiferin mainly is present in fruit, leaf, the bark of Anacardiaceae plant mango (Mangifera indica L.); The liliaceous plant wind-weed (Anemarrhena asphodeloids Bge.) rhizome, over-ground part are in the leaf of almond (Mangifera perisciformis), the fruit.
Modern pharmacology research shows that Mangiferin has anti-oxidant, and is antitumor, neuroprotective, anti-inflammatory; Bring down a fever analgesia, important physiological such as parasiticide active (Liao Hongli, Su Chunli etc., the new development of Mangiferin pharmacological research; The pharmacy practice magazine, 2008,26 (3): 161～162).Domestic existing MANGGUO ZHIKE JIAONANG, MANGGUO ZHIKE PIAN, honeysuckle flower mango capsule, the listing of Lonicera flower mango tablet preparation etc. at present, and wherein effective constituent is Mangiferin.
Mostly present disclosed Mangiferin extracting and purifying method is water extract-alcohol precipitation; Alcohol extracting macroporous resin purification method " is extracted a kind of method of Mangiferin " like patent CN100475830C " high purity mangiferin preparation method ", patent CN101759689A " a kind of preparation method of Mangiferin " and patent CN101429222A and is all adopted macroporous resin purification.Yet adopt the macroporous resin purification method, resin is with before needing processing, and purifying need pass through absorption and elution process, and the production cycle is long.When carrying out the purifying wash-out,, and cause the rate of transform to reduce because physical adsorption also causes a part of sample extremely to adsorb easily with macroporous resin.Adopt the macroporous resin purification effluent volume bigger in addition, the solvent recuperation time is long, has increased production cost, and the more waste liquid of solvent recuperation generation, and environmental protection is caused certain burden.Because the use of macroporous resin has increased the risk of introducing organic residual solvents such as benzene,toluene,xylene, vinylbenzene, alkanes, diethylbenzene class, security of products is exerted a certain influence in addition.
Summary of the invention
In view of this, the object of the invention provides a kind of preparation method of with short production cycle, Mangiferin that the rate of transform is high.
For realizing the object of the invention, the present invention adopts following technical scheme:
A kind of preparation method of Mangiferin comprises:
Step 1: contain the mixing solutions extraction of the raw material of Mangiferin with alcohol and water, filter, filtrating concentrates;
Step 2: get step 1 gained liquid concentrator and use organic solvent extraction, get that aqueous phase extracted concentrates, crystallization;
Step 3: get the mixing solutions recrystallization of step 2 gained crystal, promptly get Mangiferin with acetone and water.
Mangiferin mainly is present in fruit, leaf, the bark of Anacardiaceae plant mango; In the leaf of liliaceous plant wind-weed rhizome, over-ground part and almond, the fruit, so the fruit of mango, leaf, bark, wind-weed rhizome and the overground part material that grades all can be used as the raw material that extracts Mangiferin.Be distributed widely in province, autonomous regions such as Taiwan, Guangdong, Guangxi, Yunnan, Hainan at China's mango mango; Aboundresources, raw material is easy to get, and is cheap; Therefore, preferred mango fruit, Folium mangiferae, mango bark and wind-weed rhizome are as the raw material of preparation Mangiferin.
Mangiferin slightly is dissolved in methyl alcohol, ethanol, water, dissolves in hot dilute methanol, hot Diluted Alcohol, is insoluble to non-polar solvent.According to Mangiferin is water-solublely to be dissolved in alcoholic acid character again, and most of impurity maybe be in water with ethanol in different solubility, so adopt the alcohol and the mixing solutions of water to extract.
Wherein, as preferably, the mixing solutions of said alcohol and water is the alkanol of 1～3 carbon atom and the mixing solutions of water.
More preferably be that the alkanol of said 1～3 carbon atom and the mixing solutions of water are the alkanol of 1～3 carbon atom and 8: 2～7: 3 the mixing solutions of volume ratio of water.
Owing to contain a large amount of oil-soluble impuritieses in the Mangiferin extracting solution, after finishing, extraction at first concentrates filtering the filtrating of collecting, make solvent evaporation strength of solution increase in the solution, add organic solvent then and extract, remove oil-soluble impuritieses such as chlorophyll.
Wherein, as preferably, said simmer down to concentrated filtrate to 60 a ℃ following specific density is 1.13～1.15.
As preferably, the used organic solvent of the said organic solvent extraction of step 2 is 1: 1～3: 1 with liquid concentrator volume ratio.
More preferably be that said organic solvent is ethyl formate, ETHYLE ACETATE, butylacetate or the mixed solvent of the two arbitrarily wherein.
Mangiferin is water-soluble, and extraction back Mangiferin mainly is distributed in aqueous phase, therefore collects the aqueous phase extracted crystallization.
Wherein, as preferably, the said crystallization of step 2 is to get water after the extraction to be concentrated into 60 ℃ of following specific densities be 1.20～1.25, and leave standstill adjust pH to 1～3 then.Wherein, can select inorganic acid for adjusting pH value such as hydrochloric acid, sulfuric acid and phosphoric acid for use.
Preparing method's step 3 of Mangiferin according to the invention is further made with extra care step 2 gained crystal, adopts the mixed solvent of acetone and water to carry out recrystallization, makes the Mangiferin finished product.The mixing solutions of said acetone and water is 5: 5～7: 3 the mixing solutions of volume ratio of acetone and water.
Wherein, as preferably, said recrystallization is the mixing solutions dissolving of step 2 gained crystal with 5: 5～7: 3 acetone of volume ratio and water, crystallization.
As preferably, the preparation method of Mangiferin according to the invention, step 2 also comprise water and washing with acetone crystal successively.Said use water washing is for adding purified water wash crystallization gained crystal, and suction filtration is removed water-soluble impurity, and said use washing with acetone is for adding washing with acetone, and suction filtration is removed the impurity that is dissolved in acetone.
Wherein, as preferably, said purified water add-on is that the raw material that every 1g contains Mangiferin adds the 0.5mL purified water, and said acetone add-on is that the raw material that every 1g contains Mangiferin adds 1mL acetone.
The preparation method of Mangiferin according to the invention also comprises crystal behind water and the washing with acetone is carried out drying, makes the Mangiferin bullion.Wherein as preferred, said drying is 60 ℃ of dryings 2～4 hours.
The preparation method of Mangiferin according to the invention, step 3 comprise that also the mixing solutions recrystallization gained crystal to acetone and water carries out drying.
In the specific embodiment of the invention; The preparation method of Mangiferin according to the invention is specially raw materials such as getting mango fruit, Folium mangiferae, mango bark and wind-weed rhizome and extracts with the alkanol of 1～3 carbon atom of 8: 2～7: 3 of volume ratio and the mixing solutions of water; Filter, it is 1.13～1.15 that filtrating is concentrated into specific density.Add the organic solvent extraction of 1～3 times of volume of liquid concentrator, it is 1.20～1.25 that the water after the extraction is concentrated into specific density, and crystallization is left standstill in adjust pH to 1～3.The gained crystal is water and washing with acetone successively, and 60 ℃ of dryings made the Mangiferin bullion in 2～4 hours.Mixing solutions with 5: 5～7: 3 acetone of volume ratio and water dissolves the Mangiferin bullion down at 40 ℃～60 ℃, and every 1g Mangiferin bullion adds the mixing solutions of 80～100mL acetone and water.The activated carbon decolorizing that adds 10 times of weight of Mangiferin bullion then, remove by filter gac after, filtrating be concentrated into Mangiferin bullion mass volume ratio be 1: 10 (g/mL), leave standstill crystallization, drying makes the Mangiferin finished product.
The preparation method of Mangiferin according to the invention does not use macroporous resin purification, has avoided resin pre-treatment, absorption and elution process, has shortened the production cycle; Improved the rate of transform; And reduced the usage quantity of organic solvent, practiced thrift production cost, reduced environmental pollution.Adopt the Mangiferin purity of preparation method preparation of Mangiferin according to the invention high, do not contain benzene,toluene,xylene etc. do not meet " organic solvent of Chinese pharmacopoeia regulation, safe.
Embodiment
The embodiment of the invention discloses a kind of preparation method of Mangiferin.Those skilled in the art can use for reference this paper content, suitably improve processing parameter and realize.Special needs to be pointed out is that all similarly replace and change apparent to those skilled in the art, they all are regarded as and are included in the present invention.Method of the present invention is described through preferred embodiment, and the related personnel obviously can change or suitably change and combination method as herein described in not breaking away from content of the present invention, spirit and scope, realizes and use technology of the present invention.
In order further to understand the present invention, the preparation method of a kind of Mangiferin provided by the invention is elaborated below in conjunction with embodiment.
Embodiment 1: the preparation method of Mangiferin according to the invention prepares Mangiferin
Folium mangiferae 1Kg, drying is pulverized and is meal, adds methyl alcohol and water volume ratio and be 8: 2 mixing solutions 10L extraction 2 times; The each extraction 2 hours filtered, and merging filtrate is evaporated to the 1L volume; Specific density is ρ=1.13 (60 ℃), adds the 1L ethyl acetate extraction 2 times, and water liquid continues reclaim under reduced pressure to 0.5L; Specific density is ρ=1.20 (60 ℃), adds hydrochloric acid adjust pH to 1, leaves standstill crystallization 24 hours.Get the crystallization solution centrifugal, abandoning supernatant, deposition adds the 0.5L water washing 1 time, and suction filtration, filter cake be with 1L washing with acetone 2 times, suction filtration, filter cake obtains Mangiferin bullion 38.2 and restrains in 60 ℃ of dryings 2 hours.Getting bullion, to add 3.8L acetone and water volume ratio be 5: 5 mixing solutions, and 60 ℃ of dissolvings add 3.8 gram gacs, stir, and suction filtration, filtrate decompression is concentrated into 0.38L, crystallization 12 hours, suction filtration is drying to obtain Mangiferin finished product 34.3 grams.
Embodiment 2: the preparation method of Mangiferin according to the invention prepares Mangiferin
Folium mangiferae 1Kg, drying is pulverized and is meal, adds propyl alcohol and water volume ratio and be 7: 3 mixing solutions 15L extraction 3 times; The each extraction 1 hour filtered, and merging filtrate is evaporated to the 1L volume; Specific density is ρ=1.15 (60 ℃), adds butylacetate 3L extraction 3 times, and water liquid continues reclaim under reduced pressure to the 0.5L volume; Specific density is ρ=1.23 (60 ℃), adds hydrochloric acid adjust pH 3, leaves standstill crystallization 12 hours.Get the crystallization solution centrifugal, abandoning supernatant, deposition adds the 0.5L water washing 1 time, and suction filtration, filter cake be with 1L washing with acetone 3 times, suction filtration, filter cake obtains Mangiferin bullion 37.3 and restrains in 60 ℃ of dryings 4 hours.Getting bullion, to add 3.7L acetone and water volume ratio be 6: 4 mixing solutions, and 40 ℃ of dissolvings add 3.7 gram gacs, stir, and suction filtration, filtrate decompression is concentrated into 0.37L, crystallization 24 hours, suction filtration is drying to obtain Mangiferin finished product 33.5 grams.
Embodiment 3: the preparation method of Mangiferin according to the invention prepares Mangiferin
Folium mangiferae 1Kg, drying is pulverized and is meal, adds ethanol and water volume ratio and be 8: 2 mixing solutions 10L extraction 3 times; The each extraction 2 hours filtered, and merging filtrate is evaporated to the 1L volume; Specific density is ρ=1.14 (60 ℃), and the mixed solvent 1L that adds ethyl formate and ETHYLE ACETATE extracts 2 times, and water liquid continues reclaim under reduced pressure to the 0.5L volume; Specific density is ρ=1.25 (60 ℃), adds hydrochloric acid adjust pH 2, leaves standstill crystallization 18 hours.Get the crystallization solution centrifugal, abandoning supernatant, deposition adds the 0.5L water washing 1 time, and suction filtration, filter cake be with 1L washing with acetone 2 times, suction filtration, filter cake obtains Mangiferin bullion 39.4 and restrains in 60 ℃ of dryings 3 hours.Getting bullion, to add 3.9L acetone and water volume ratio be 7: 3 mixing solutions, and 60 ℃ of dissolvings add 3.9 gram gacs, stir, and suction filtration, filtrate decompression is concentrated into 0.39L, crystallization 24 hours, suction filtration is drying to obtain Mangiferin finished product 34.8 grams.
Embodiment 4: adopt the macroporous resin purification legal system to be equipped with Mangiferin
Be equipped with Mangiferin according to the macroporous resin purification legal system, get Folium mangiferae 1Kg, drying is pulverized and is meal; Adding methyl alcohol and water volume ratio are that 8: 2 mixing solutions 10L extracts 2 times, extract 2 hours at every turn, filter merging filtrate; Being evaporated to does not have the alcohol flavor, and last D101 macroporous resin wash-out with water, 20% ethanolic soln, the 70% ethanolic soln wash-out of 5 times of column volumes, is collected 70% ethanol eluate respectively; Being evaporated to does not have the alcohol flavor, leaves standstill crystallization, obtains Mangiferin bullion 28.8 grams.Getting bullion, to add 2.9L acetone and water volume ratio be 5: 5 mixing solutions, and 60 ℃ of dissolvings add 2.9 gram gacs, stir, and suction filtration, filtrate decompression is concentrated into 0.29L, crystallization 12 hours, suction filtration is drying to obtain Mangiferin finished product 25.9 grams.
Embodiment 5: the comparison test of Mangiferin content
Measure Mangiferin content according to HPLC (2010 version " an appendix VI of Chinese pharmacopoeia D).Strong to close silica gel be weighting agent with octadecylsilane; With methyl alcohol-0.2% phosphoric acid solution (30: 70) is moving phase; The detection wavelength is 240nm.Theoretical plate number must not calculate by the Mangiferin peak and is lower than 3000.
1, the preparation of reference substance solution
It is an amount of to get the Mangiferin reference substance, and accurate the title decides, and adds 50% methyl alcohol and processes the solution that contains 25 μ g among every 1ml, filters with millipore filtration (0.45 μ m), gets filtrating, promptly gets.
2, the preparation of sample solution
Get the Mangiferin of embodiment 1～4 preparation, accurate respectively title is fixed, adds 50% methyl alcohol and processes the solution that contains 25 μ g among every 1ml, filters with millipore filtration (0.45 μ m), gets filtrating, promptly gets.
3, assay method
Accurate respectively reference substance solution and each 10 μ l of sample solution of drawing inject high performance liquid chromatograph, measure Mangiferin content, and calculate the rate of transform of Mangiferin, and the result sees table 1.Wherein, the rate of transform is calculated as follows:
Mangiferin content * 100% in Mangiferin content/finished product in the rate of transform=raw material
The comparison test of table 1 Mangiferin content
Can know that by table 1 result embodiment 1～3 all reaches more than 97% according to the Mangiferin finished product Mangiferin purity of preparing method's preparation according to the invention, and the Mangiferin rate of transform also all reaches more than 77% in the Folium mangiferae; And be equipped with the Mangiferin finished product according to the macroporous resin purification legal system; Mangiferin purity is merely 96.2%, and total rate of transform only has 59%, shows the preparation method of Mangiferin according to the invention; The Mangiferin rate of transform is high, and the Mangiferin purity of preparation is high.
The explanation of above embodiment just is used for helping to understand method of the present invention and core concept thereof.Should be pointed out that for those skilled in the art, under the prerequisite that does not break away from the principle of the invention, can also carry out some improvement and modification to the present invention, these improvement and modification also fall in the protection domain of claim of the present invention.
Claims (10)
1. the preparation method of a Mangiferin comprises:
Step 1: contain the mixing solutions extraction of the raw material of Mangiferin with alcohol and water, filter, filtrating concentrates;
Step 2: get step 1 gained liquid concentrator and use organic solvent extraction, get the aqueous phase extracted crystallization;
Step 3: get the mixing solutions recrystallization of step 2 gained crystal, promptly get Mangiferin with acetone and water.
2. preparation method according to claim 1 is characterized in that, the mixing solutions of said alcohol and water is the alkanol of 1～3 carbon atom and the mixing solutions of water.
3. preparation method according to claim 2 is characterized in that, the alkanol of said 1～3 carbon atom and the mixing solutions of water are the alkanol of 1～3 carbon atom and 8: 2～7: 3 the mixing solutions of volume ratio of water.
4. preparation method according to claim 1 is characterized in that, the said simmer down to concentrated filtrate of step 1 to specific density is 1.13～1.15.
5. preparation method according to claim 1 is characterized in that, said organic solvent is 1: 1～3: 1 with liquid concentrator volume ratio.
6. preparation method according to claim 5 is characterized in that, said organic solvent is ethyl formate, ETHYLE ACETATE, butylacetate or the mixed solvent of the two arbitrarily wherein.
7. preparation method according to claim 1 is characterized in that, the said crystallization of step 2 is 1.20～1.25 for the water after extracting is concentrated into specific density, and leave standstill adjust pH to 1～3.
8. preparation method according to claim 1 is characterized in that, the mixing solutions of said acetone of step 3 and water is 5: 5～7: 3 the mixing solutions of volume ratio of acetone and water.
9. preparation method according to claim 8 is characterized in that, said recrystallization is the mixing solutions dissolving of step 2 gained crystal with 5: 5～7: 3 acetone of volume ratio and water, crystallization.
10. preparation method according to claim 1 is characterized in that, step 2 also comprises water and washing with acetone crystal successively.
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| CN105820158A (en) * | 2015-01-08 | 2016-08-03 | 昆明制药集团股份有限公司 | Method for extracting mangiferin |
| CN106831738A (en) * | 2017-01-23 | 2017-06-13 | 攀枝花学院 | It is a kind of that the method for separating mangiferin is extracted from mango leaf |
| CN107266509A (en) * | 2017-07-20 | 2017-10-20 | 广西南宁桂知科技有限公司 | The technique that a kind of use mango leaf produces mangiferin |
| CN108239079A (en) * | 2016-12-23 | 2018-07-03 | 中国医学科学院药物研究所 | Mangiferin V type substance of crystalline substance and preparation method and its composition and purposes |
| CN108239080A (en) * | 2016-12-23 | 2018-07-03 | 中国医学科学院药物研究所 | Mangiferin VI type substance of crystalline substance and preparation method and its composition and purposes |
| CN111423424A (en) * | 2020-01-20 | 2020-07-17 | 中国热带农业科学院分析测试中心 | Preparation method of high-purity mangiferin crystal |
| TWI702047B (en) * | 2018-07-06 | 2020-08-21 | 大江生醫股份有限公司 | Use of mango extracts and bioactive ingredients obtained therefrom for reducing fat accumulation and oxidative damage in liver |
| CN113416182A (en) * | 2021-05-28 | 2021-09-21 | 西安金泰生物技术有限公司 | Mangiferin and preparation method thereof |
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| CN105820158B (en) * | 2015-01-08 | 2019-01-29 | 昆药集团股份有限公司 | A method of extracting mangiferin |
| CN105820158A (en) * | 2015-01-08 | 2016-08-03 | 昆明制药集团股份有限公司 | Method for extracting mangiferin |
| CN108239079B (en) * | 2016-12-23 | 2021-07-06 | 中国医学科学院药物研究所 | Mangiferin crystal V-shaped substance, preparation method, composition and application thereof |
| CN108239079A (en) * | 2016-12-23 | 2018-07-03 | 中国医学科学院药物研究所 | Mangiferin V type substance of crystalline substance and preparation method and its composition and purposes |
| CN108239080A (en) * | 2016-12-23 | 2018-07-03 | 中国医学科学院药物研究所 | Mangiferin VI type substance of crystalline substance and preparation method and its composition and purposes |
| CN108239080B (en) * | 2016-12-23 | 2021-09-10 | 中国医学科学院药物研究所 | Mangiferin crystal VI substance, preparation method, composition and application thereof |
| CN106831738B (en) * | 2017-01-23 | 2020-01-07 | 攀枝花学院 | Method for extracting and separating mangiferin from mango leaves |
| CN106831738A (en) * | 2017-01-23 | 2017-06-13 | 攀枝花学院 | It is a kind of that the method for separating mangiferin is extracted from mango leaf |
| CN107266509A (en) * | 2017-07-20 | 2017-10-20 | 广西南宁桂知科技有限公司 | The technique that a kind of use mango leaf produces mangiferin |
| TWI702047B (en) * | 2018-07-06 | 2020-08-21 | 大江生醫股份有限公司 | Use of mango extracts and bioactive ingredients obtained therefrom for reducing fat accumulation and oxidative damage in liver |
| CN111423424A (en) * | 2020-01-20 | 2020-07-17 | 中国热带农业科学院分析测试中心 | Preparation method of high-purity mangiferin crystal |
| CN111423424B (en) * | 2020-01-20 | 2021-12-14 | 中国热带农业科学院分析测试中心 | Preparation method of high-purity mangiferin crystal |
| CN113416182A (en) * | 2021-05-28 | 2021-09-21 | 西安金泰生物技术有限公司 | Mangiferin and preparation method thereof |
| CN113416182B (en) * | 2021-05-28 | 2022-03-29 | 西安金泰生物技术有限公司 | Mangiferin and preparation method thereof |
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Address after: 650100 Kunming science and Technology Industrial Development Zone, Yunnan Province Road No. 166 Patentee after: Kun Yao Group Plc Address before: 650100 Kunming science and Technology Industrial Development Zone, Yunnan Province Road No. 166 Patentee before: Kunming Pharmaceutical Industry Group Corp., Ltd. |